Holiday houses in Oakland City

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines CABIN!! We are 12 miles from Holiday World (11 if you take back roads). For the 2025 season the cabin no longer includes the pool. It does however have its own private hot tub (as of May 1st, 2025). Cabin includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option).

Fabulous on Historic First St. Near Haynies Corner

Light and airy with 11ft ceilings and warm wood floors, this 900 sq foot updated downtown 1 bedroom is just right for your next visit to Evansville. Whether you are in town for work or for play, this is a great spot for you. Located in the same block as Haynies Corner, two blocks from the river trail, and very close to Main Street, Ford Center and Old National events Plaza this home provides a great spot for the active life as well as the night life. Fully equipped, stainless appliances.

Princeton Place | QUEEN 2BD/1BA Apt

Be our guest in this 2-bedroom, 1-bathroom apartment just minutes from TMMI (TOYOTA) and all the restaurants and amenities in Princeton. This is a simple, affordable option ideal for traveling professionals who want more than just a hotel stay. 🛌 What You’ll Enjoy: 🛏️ 2 comfortable bedrooms 🚿 1 clean, functional bathroom 🧺 In-unit washer and dryer ⚡ Fast, reliable Wi-Fi 🍽️ Fully stocked kitchen 🚗 Free street parking 📍 Convenient location near TOYOTA and Princeton

College Town Comfort

Our 2-bedroom apartment is located in close proximity to Oakland City University. This family friendly retreat offers a cozy and inviting atmosphere for you and your loved ones. With ample space, modern amenities, and a convenient location, it’s the perfect place to relax after a day of exploring the campus and nearby attractions. Whether you’re visiting for a college tour or a business trip, our apartment provides the comfort and convenience you need for an enjoyable getaway.

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

Best Value/Sleeps 4/ Cozy/Center Town /Pets ok!

This is a private unit, but There is a GUEST SUITE attached to this listing (also available on Air BNB.) However, there are NO shared spaces. Each listing has a separate entrance. Near shopping, restaurants. 1Bedroom-2 queen beds-1bath cable/wifi, stocked wi/ snacks & amenities. Key lock box entry, Washer/Dryer. Couch folds down with a pull out feature on the base see pics or contact us to operate.

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. 2 complimentary drip coffees are included with your stay.